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Updated: Jul 4, 2025

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
Protection-Free, Two-step Synthesis of C5-C Functionalized Pyrimidine Nucleosides
Karolina Podskoczyj1, Anna Kuszczynska1, Agnieszka Dziergowska1
1Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Lodz, Poland.
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A simple, reliable, and efficient method for the gram-scale chemical synthesis of pyrimidine nucleosides functionalized with C5-carboxyl, nitrile, ester, amide, or amidine, starting from unprotected uridine and cytidine, is described. The protocol involves the synthesis of 5-trifluoromethyluridine and 5-trifluoromethylcytidine with Langlois reagent (CF3 SO2 Na) in the presence of tert-butyl hydroperoxide and subsequent transformation of the CF3 group to the C5-C 'carbon substituents' under alkaline conditions. © 2024 Wiley Periodicals LLC. Basic Protocol 1: Synthesis and characterization of 5-trifluoromethyluridine (5-CF3 U) and 5-trifluoromethylcytidine (5-CF3 C) Basic Protocol 2: Conversion of 5-CF3 U and 5-CF3 C to several C5-substituted ribonucleosides.
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